It does look as if it is being used as a cheap and likely risky air taxi.
Some pilots are just certified, with scary low hours - I am guessing that they do not own the airplanes and likely only fly when they get a 'punter'.
I actually signed up to it, to see what it is like and how it works - got connected to a couple for my usual Sunday morning circuit of the island - I own the airplane, it takes 30 minutes or so and Avgas is US7.50 a gallon, so marginal cost about $12 each, plus they would have the Wingly fees on top - I didn't give Wingly my bank details so I didn't take the money.
It was as fun trip, they got to see the island from the air, spotted the flying club's 172 zoom by and a Boeing heavy freighter on short final as we joined the circuit. At the time I had about 300 hours, a couple of hundred in the airplane, in a very benign environment with which I am very familiar, in near perfect weather, constant flight following - but I thought even during the flight, what if I were lower hours, in an unfamiliar rental, on an unfamiliar route, in less perfect weather, with serious expectations of my passengers to get to their destination. Then my weirdest thought, a good way for a couple of strangers to commit suicide - but then I do tend to see the downside of things.
Now here it gets even weirder - I am a VFR only pilot, no plans for an IR, but quite like the idea of doing a a commercial non-IR which the FAA have - that would mean I can only fly 50 miles or so from the airport with passengers. To do a VFR only commercial one must have 250 hours - this is a rule of an aviation authority which EASA thinks doesn't have such good standards as EASA, which has determined that 250 hours is the minimum number of hours and then after additional training will limit one to 50 mile trips - not Wingly type adverts as that is holding out.
So singluarly unimpressed that Wingly does not have a minimum number of total hours and hours on type.
Still waiting for the first Wingly passenger death - there is a suggestion that the Channel crash, although not a Wingly flight, had some of the characteristics i.e. a not legitimately certified pilot, low on currency in an unfamiliar airplane (the armchair pundits are postulating not running the pitot heat during the flight, the story does that the POH says on all the time in the conditions of the flight).
I do agree with the idea that it there is always risk, it seems that renter's insurers have determined that it is too great, so no Wingly flights (likely to renters concerned about their vicarious liability) - I banned a renter from renting my airplane six years ago when I found the surprising number of "friends" she was flying down to Union were yacthies paying a small fortune for the flights (px in my Archer their luggage in her Archer - seems mine was deemed better maintained!). As an aside, her Archer was the one that was written off on Richard Terrelonge's off airport landing five years ago when the engine quit turning base, and her Seneca likewise when the gear failed and it belly landing here.
While not a fan of regulation I do think that Wingly type flights should require airplanes be maintained to commercial standards (100hr inspections), that the pilots should have 100hrs post PPL, 10 hours in the type, under take some form of training in managing strangers in the airplane, some document to show to Wingly that they meet those requirements.